Holiday Homes in Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 June - 14 June
In three months
10 July - 12 July
In four months
7 Aug - 9 Aug

Top Cities in Maryland

Holiday HomesHoliday Homes

Frederick

Frederick

Our top choices for Maryland holiday homes

Exterior

Hard to find, beautiful 4 bedroom luxury villa

Hard to find, beautiful 4 bedroom luxury villa
North Ocean City
9.0 out of 10, Wonderful, (29 reviews)
"It was a very nice place to stay. Shuttle busses were a 2 minute walk. We had a great time."
United States
Thomas T.
Hard to find, beautiful 4 bedroom luxury villa
Fridge, microwave, oven, stovetop

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Historic District
10.0 out of 10, Exceptional, (33 reviews)
"Such a cute house and a short walk to all the shops and restaurants. "
United States
Ty M.
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Fridge, microwave, oven, stovetop

Affordable Luxury Town Home in Federal Hill Baltimore.

Affordable Luxury Town Home in Federal Hill Baltimore.
Riverside
9.4 out of 10, Exceptional, (73 reviews)
"Great location. Host responded quickly to my questions. "
United States
Ann K.
Affordable Luxury Town Home in Federal Hill Baltimore.
Exterior detail

Charming 2-bedroom townhome with WiFi, AC in awesome Fells Point Baltimore

Charming 2-bedroom townhome with WiFi, AC in awesome Fells Point Baltimore
Fells Point
9.8 out of 10, Exceptional, (36 reviews)
"We enjoyed our stay. House was clean and comfortable. Loved the location. "
United States
Jennifer C.
Charming 2-bedroom townhome with WiFi, AC in awesome Fells Point Baltimore
Sun-loungers, beach towels

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (151 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is AU$737
includes taxes & fees
21 Apr - 22 Apr
5-bedroom vacation home 5 minutes from historic Charlestown
Exterior

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier
Cambridge
9.6 out of 10, Exceptional, (89 reviews)
"The host, Virgina, was amazing, so accommodating. Beautiful property. Looking forward to hopefully booking next year. "
United States
Susan B.
Private 2 Acre Waterfront Family Retreat with Pool & Pier
Interior

Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!

Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
Downtown Ocean City
10.0 out of 10, Exceptional, (22 reviews)
"Great vacation area and accommodation!"
United States
Letizia
Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
Property grounds

Captivating Chesapeake experience

Captivating Chesapeake experience
Perryville
10.0 out of 10, Exceptional, (286 reviews)
"Beautiful and peaceful spot! Great long weekend getaway."
United States
Elizabeth J.
Captivating Chesapeake experience
Exterior

Fed Hill w Deck Walk Score 95 Steps from Harbor

Fed Hill w Deck Walk Score 95 Steps from Harbor
Federal Hill
9.0 out of 10, Wonderful, (44 reviews)
"Great location. Nice home. "
United States
kim s.
The price is AU$600
includes taxes & fees
29 Apr - 30 Apr
Fed Hill w Deck Walk Score 95 Steps from Harbor
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.0 out of 10, Wonderful, (84 reviews)
"Great location and very comfortable. Definitely will consider for future trips to this area."
United States
Jon E.
The price is AU$423
includes taxes & fees
13 May - 14 May
Luxury Condo In Downtown Frederick
Terrace/patio

Historic Annapolis Home 1.5 blocks from center of town.

Historic Annapolis Home 1.5 blocks from center of town.
Historic District
9.8 out of 10, Exceptional, (47 reviews)
"We had another great stay! Great location and great host!"
United States
Liz D.
Historic Annapolis Home 1.5 blocks from center of town.
Terrace/patio

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Oakland
8.2 out of 10, Very good, (74 reviews)
"Very convenient, excellent hosts."
United States
Jim S.
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Beach nearby, sun-loungers

Come Hang at the Treehouse!

Come Hang at the Treehouse!
Midtown Ocean City
10.0 out of 10, Exceptional, (35 reviews)
"Gorgeous place with wonderful views !! "
United States
Susan H.
Come Hang at the Treehouse!
Property grounds

New Listing! Beautiful 4 bedroom oceanfront townhome

New Listing! Beautiful 4 bedroom oceanfront townhome
Midtown Ocean City
8.4 out of 10, Very good, (6 reviews)
"We loved this place. Its location on the beach is its best feature. It’s also located close to lots of nice places in OC. We are a family of 11 with 3 married kids and 3 grandchildren. The large house provided nice space for everyone. We loved the decks on every level. "
United States
James A.
New Listing! Beautiful 4 bedroom oceanfront townhome
Fridge, microwave, oven, stovetop

Sweet Bamboo Beach Cottage

Sweet Bamboo Beach Cottage
north beach
9.8 out of 10, Exceptional, (84 reviews)
"The beach house was cute, well equipped and in good repair. Made for a cozy Christmas. Would come back to stay again."
United States
Kathleen S.
Sweet Bamboo Beach Cottage
Property grounds

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Easton
10.0 out of 10, Exceptional, (99 reviews)
"The host was lovely. Very responsive, thoughtful and welcoming!The home was perfect for our get away. It was better than the photos, comfy with a well appointed kitchen!"
United States
lori l.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Dining

3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.

3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.
Silver Spring
10.0 out of 10, Exceptional, (58 reviews)
"This was a great stay, thank you so much for allowing us to stay at your place."
United States
Rowland
3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.
Dining

BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!

BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!
North Ocean City
9.6 out of 10, Exceptional, (68 reviews)
"The place was beautiful , convenient to walk around to the beach and the stores "
United States
Theresa K.
BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!
Exterior

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Eastport
10.0 out of 10, Exceptional, (134 reviews)
"Great property and location. "
United States
Steve N.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Exterior

Sunset Island is Loved for it's Amazing Amenities

Sunset Island is Loved for it's Amazing Amenities
North Ocean City
9.4 out of 10, Exceptional, (13 reviews)
"Loved the house and enjoyed our stay to celebrate NYE."
United States
Todd P.
Sunset Island is Loved for it's Amazing Amenities
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Maryland Hotel Reviews

The Bethesdan Hotel, Tapestry Collection by Hilton

The Bethesdan Hotel, Tapestry Collection by Hilton

8/10 Good
"Hotel was clean and in good condition "
Thanarat 4-night trip
Posted 3 hours ago
The Bethesdan Hotel, Tapestry Collection by Hilton

Find out more about Maryland

Maryland Holiday Homes information

Number of reviews
1,325
Accommodation
4667 Holiday Homes
Lowest Price
AU$423
Highest Price
AU$737

Explore a world of travel with Expedia